Ethyl cyanoacetate → HCID 68871582, compound

HRID 1986351Notes

Reaction equation

[NH2:1][C:2]1[C:3]([NH:19][C:20]2[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=2)=[CH:4][C:5]([O:8][C:9]2[CH:10]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1.[C:27]([CH2:29][C:30](OCC)=O)#[N:28]>>[C:27]([CH2:29][CH:30]1[NH:1][C:2]2[CH:7]=[N:6][C:5]([O:8][C:9]3[CH:10]=[C:11]([NH:15][C:16](=[O:18])[CH3:17])[CH:12]=[CH:13][CH:14]=3)=[CH:4][C:3]=2[N:19]1[C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)#[N:28]

Participants

Reactant 2

HCID 7764Ethyl cyanoacetate

HCID 68868411HCID 68868411, compound

Product 1

HCID 68871582HCID 68871582, compoundYield 78%

Conditions

Temperature: 195 °C

Procedure

The product from Step 3 (2.9 g, 8.3 mmol) and ethyl cyanoacetate (6 mL) were combined and heated to 195° C. in a sealed tube. The reaction mixture was cooled and the crude material was purified by chromatography (0-10% methanol in EtOAc) to give the title compound (2.6 g, 78%). MS (ES+) m/e 400 [M+H]+.

Workup

temperatureThe reaction mixture was cooled
customthe crude material was purified by chromatography (0-10% methanol in EtOAc)

Sources & evidence

ORD record: ord-ee73259e805a4e0888717ea13b2b50ba
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547779B2

Reaction notes

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